(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

Base Information

Chemical Name:(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone
CAS No.:903522-54-3
Molecular Formula:C₂₉H₅₆O₄Si
Molecular Weight:496.847
Hs Code.:

Synonyms:(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

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Chemical Property of (2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

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Technology Process of (2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

There total 7 articles about (2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

: (2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-[(S)-2-(dimethyl-hydrazono)-1-methyl-ethoxy]-4-((Z)-heptadec-10-enyl)-4-hydroxy-cyclohexanone

: 903522-54-3
(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

Guidance literature:: With chloro-trimethyl-silane; In dichloromethane; for 4h;
DOI:10.1021/ol061000s

Reference yield:

: 903522-42-9
(3S,4aR,8aR)-8a-((Z)-Heptadec-10-enyl)-3-methyl-4a,8a-dihydro-5H-benzo[1,4]dioxine-2,6-dione

: 903522-54-3
(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: RhCl(PPh₃)3 / benzene / 2 h

1.2: 84 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / 0 °C

2.1: 66 percent / DMAP / dimethylformamide / 20 °C

3.1: Dibal-H / tetrahydrofuran / 0.5 h / -78 °C

4.1: 51.1 mg / TFA / CH₂Cl₂ / 20 °C

5.1: 78 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 1 h / 20 °C

6.1: 50 percent / TMSCl / CH₂Cl₂ / 4 h

With dmap; chloro-trimethyl-silane; tetrapropylammonium perruthennate; 4 A molecular sieve; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; RhCl(PPh₃)3; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol061000s

Reference yield:

: 903522-51-0
(3S,4aS,8aR)-5-Bromo-8a-((Z)-heptadec-10-enyl)-3-methyl-4a,8a-dihydro-5H-benzo[1,4]dioxine-2,6-dione

: 903522-54-3
(2S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-4-((Z)-heptadec-10-enyl)-4,5-dihydroxy-cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 85 percent / NaI; TMSI / acetonitrile / 4 h

2.1: RhCl(PPh₃)3 / benzene / 2 h

2.2: 84 percent / dimethyldioxirane / CH₂Cl₂ / 1 h / 0 °C

3.1: 66 percent / DMAP / dimethylformamide / 20 °C

4.1: Dibal-H / tetrahydrofuran / 0.5 h / -78 °C

5.1: 51.1 mg / TFA / CH₂Cl₂ / 20 °C

6.1: 78 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves; TPAP / CH₂Cl₂ / 1 h / 20 °C

7.1: 50 percent / TMSCl / CH₂Cl₂ / 4 h

With dmap; chloro-trimethyl-silane; tetrapropylammonium perruthennate; trimethylsilyl iodide; 4 A molecular sieve; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; trifluoroacetic acid; sodium iodide; RhCl(PPh₃)3; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ol061000s